Round: 25 Ground: Hardcourt outdoor
| Davis Cup | 2016/07/17 19:20 | Rudy Richter v Santiago Maresca | 7-6,7-6 |
| ITF Mexico F5 | 2016/05/31 19:00 | Rudy Richter v Alejandro Gomez | 0-6,2-6 |
| ITF Mexico F4 | 2016/05/24 16:00 | Ricky Medinilla v Rudy Richter | 6-2,6-3 |
| ITF Mexico F4 | 2016/05/22 16:30 | Rudy Richter v Juan Montes | 7-6,6-2 |
| ITF Mexico F3 | 2016/05/15 17:30 | Rudy Richter v Raul-Isaias Rosas-Zarur | 3-6,2-6 |
| ITF Mexico F3 | 2016/05/14 14:30 | Emiliano Elizarraras v Rudy Richter | 0-6,0-6 |
| ITF USA F13 Qual | 2016/04/10 15:00 | Rudy Richter v Robert Levine | 1-6,1-6 |
| ITF USA F13 Qual | 2016/04/09 16:30 | Constantinos Papavasiliou v Rudy Richter | 0-6,0-6 |
| ITF Canada F9 Qual | 2016/09/22 17:15 | Adam El Mihdawy v Raleigh Smith | 3-6,6-4,6-2 |
| ITF Canada F9 Qual | 2016/09/21 15:20 | Hans Hach Verdugo v Raleigh Smith | 3-6,5-7 |
| ITF Canada F8 | 2016/09/15 16:50 | Raleigh Smith v Filip Peliwo | 4-6,3-6 |
| ITF Canada F8 | 2016/09/14 14:00 | Francis Casey Alcantara v Raleigh Smith | 4-6,4-6 |
| ITF Canada F8 | 2016/09/13 16:15 | David Volfson v Raleigh Smith | 5-7,1-6 |
| ITF Canada F7 | 2016/09/06 16:10 | Frank Dancevic v Raleigh Smith | 6-1,6-2 |
| ITF Canada F6 | 2016/08/31 18:30 | Raleigh Smith v Stefanos Tsitsipas | 6-7,5-7 |
| ITF Canada F6 | 2016/08/29 16:00 | Raleigh Smith v Antoine Leduc | 6-3,6-0 |